Triphenylphosphine → Ethyl 3-(chloromethyl)-5-(dimethylamino)benzoate

HRID 2368874노트

반응식

HRID 2368874 반응식
[CH3:1][N:2]([CH3:16])[C:3]1[CH:4]=[C:5]([CH:11]=[C:12]([CH2:14]O)[CH:13]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C(=O)N([Cl:43])C(=O)C1>C(Cl)Cl>[Cl:43][CH2:14][C:12]1[CH:11]=[C:5]([CH:4]=[C:3]([N:2]([CH3:16])[CH3:1])[CH:13]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7]

참가 물질

5

반응물 3

HCID 11776TriphenylphosphineHCID 31398ChlorosuccinimideHCID 68335184Ethyl 3-(dimethylamino)-5-(hydroxymethyl)benzoate

생성물 1

HCID 68335175Ethyl 3-(chloromethyl)-5-(dimethylamino)benzoate수율 96%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of Compound 2 (3.45 g, 15.452 mmol) and PPh3 (6.14 g, 23.17 mmol) in 70 mL of DCM was added NCS (3.19 g, 23.178 mmol) at 0° C. The reaction mixture was stirred for 1.5 hours. After removal of solvent under reduced pressure, the residue was dissolved in Et2O. The solution was washed with brine and dried with MgSO4. The solution was filtered and concentrated. The residue was subjected to chromatography over silica gel (Hexanes/EtOAc=9.5/0.5) to give Compound 3 (3.585 g, 96%). 1H-NMR (500 MHz, CDCl3) δ 7.38 (s, 1H), 7.35 (s, 1H), 6.89 (s, 1H), 4.57 (s, 2H), 4.37 (q, J=7.1 Hz, 2H), 3.00 (s, 6H), 1.39 (t, J=7.1 Hz, 3H); 13C-NMR (125 MHz, CDCl3) δ 166.73, 150.63, 138.35, 131.59, 117.31, 116.20, 113.22, 60.95, 46.40, 40.43, 14.31; ESI-MS: m/z (MH+): 242.0942 (calc'd), 242.0944 (found).

후처리

  1. customAfter removal of solvent under reduced pressure
  2. dissolutionthe residue was dissolved in Et2O
  3. washThe solution was washed with brine
  4. dry with materialdried with MgSO4
  5. filtrationThe solution was filtered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-64a0cd2b68f24191bab7483321b13776
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08703815B2

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